


Mother Knows Best

by AshwinMeird



Category: Supernatural
Genre: Absent Chuck, Alternate Universe, And Not Living Up To Them, Candy Store Owner Gabriel (Supernatural), Castiel's Family is Rich (Supernatural), Established Castiel/Dean Winchester, Expectations, F/M, Family Drama, Gay Castiel, I Think I Try To Be Funny, M/M, Morally Grey Naomi, Mother-Son Relationship, Overbearing Mother, POV Naomi Milton, POV Outsider, Religious Themes
Language: English
Status: Completed
Published: 2020-11-17
Updated: 2020-11-17
Packaged: 2021-03-10 03:22:13
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,628
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27567442
Author URL: https://archiveofourown.org/users/AshwinMeird/pseuds/AshwinMeird
Summary: Naomi Milton is a self made woman, she grew her business and raised her four sons after she told her (ex) husband Chuck to exit their lives.  Now years later her four sons, whom she taught the best and proper way to live to, visit for a Christmas dinner that show Naomi just how little she actually knows about her sons.
Relationships: Castiel/Dean Winchester, Gabriel/Kali (Supernatural), Michael/Hannah (Supernatural), Naomi Milton/Chuck Shurley
Comments: 14
Kudos: 104





	Mother Knows Best

**Author's Note:**

> This isn't meant to be overly fluffy or nice, it's my attempt at writing from a not strictly nice POV. This is not a redemption arc, Naomi is a vehicle used to make a point. If anything in the fic offends you or anything please let me know down in the comments.
> 
> This is just my commentary on what some families/family expectations can be, not my opinions on most things in this fic.

Naomi Milton may have made some questionable choices marrying Chuck Shurley, but if it brought her one thing it was her sons.

Naomi met Chuck when they were young and naive. Naomi didn’t come from much; her mother was absent most of her childhood and her father made a decent living for the three of them. Chuck, however, came from a well off family with a hotel chain that had been founded almost 100 years before the two of them met.

They married less than a year after meeting in a religious ceremony.

Naomi was a very intelligent woman, not long after they got married Chuck told her of his disillusionment with running the company. Naomi decided to take on the CEO position herself and Chuck focused on his writing career.

Michael was born shortly after, followed by his three younger brothers. Naomi had hoped for a daughter, but she could always help her sons find good strong wives.

She should have known things would not continue on the path of good fortune.

She knew her marriage to Chuck was not well, she had spoken to the local pastor about it after several Sunday Masses about his drinking and the fights they would have when the boys weren’t around. She was ready to ask for counseling when she arrived back to their home after picking up the two older boys from their Catholic Elementary School.

“What are these?” She asked, putting baby Castiel’s carrier on the ground beside her.

Chuck sighed at her, “Divorce papers, I can’t do this anymore.”

“Think about the boys, Chuck. What will it do to them having you gone?”

“I’m not leaving them Naomi, I just cannot be with you anymore. I don’t like the person being around you makes me.”

“No Chuck, I think that we can make this work, but if you cannot do that for our family I think it’s best that you leave.”

That was the last time she saw Chuck Shurley. Most of the assets involved in the divorce wouldn’t be fought over; Naomi already owned the company, her car, and the house, and everything else needn’t be fought over. It was an amicable split and Chuck, unnecessarily, sent child support every month.

Naomi tried dating several times over the years, one man named Joshua even made it as far as meeting Gabriel, unintentionally, before they decided that they did not work as a couple.

At work she spent the better part of a decade completing a complete overhaul of the hotel company. She hired and promoted the best people to create new policies and business practices so that the company was over doubling its profit from the years prior to her ownership. Now Milton Luxury Hotels, as she renamed it, had locations in 12 states and 14 countries worldwide.

Naomi focused on her boys. She wanted to raise them right.

They all attended proper Catholic schools and were on their ways to having formidable jobs.

In recent years, though Naomi was only 57, Naomi spent most of her time alone in her fancy house outside of Boston. It was almost Christmas which meant her four boys would soon be there to visit for the holidays.

*~*~*~*~*~*

Michael was the first to arrive. He was her oldest, she and him got along the best of all of his siblings. He always came to her when he needed help and she happily aided him.

Michael graduated high school and college top of his class. He, by her advice, got a business degree so that at 55 Naomi was able to retire early and hand Milton Luxury Hotels down to him.

“Michael, it is lovely to see you,” Naomi greeted wrapping her son in a hug.

Michael looked confused for a moment after the hug ended but quickly replied, “You as well Mother.”

“Now who is this?” Naomi turned towards the lovely brunette standing in the doorway behind him.

The girl stepped forward, extending a hand towards Naomi. “My name is Hannah Johnson.”

‘Hannah’ gave her eldest a look before Michael added, “She is my fiance, Mother.”

The smile on her face became forced in an instance. “Michael,” She began only to be cut off.

“Why don’t you two talk for a bit,” Hannah suggested, then turned towards Michael, “I’ll grab our stuff from the car, Hael’s expecting my call now that we’ve arrived anyways.”

Michael nodded and allowed his fiance to exit before following his mother into the first sitting room.

“Michael,” Naomi tried again, “Why is this the first I’m hearing about this woman you’re engaged to? What ever happened to Hael?”

Hael was a well off girl, the daughter of a state senator, that lived not far from Michael’s residence at the Milton Columbus. Naomi introduced them at a dinner party before she retired.

“Hael was a wonderful woman, Mother but,” Michael started.

“But what? She was wealthy, smart, already a well known journalist, you would have made an excellent pair.”

“She just wasn’t right for me. I am sorry if this displeases you, but I would love for you to get to know Hannah. I think you’ll find her quite acceptable for me.” 

Michael gave her a pleading look. He was never one to ask for much, so Naomi decided to humor him and meet this woman. If it didn’t work out she could always help him find a more suitable partner like she had when she introduced Lucifer to Lillith.

As it turned out, she really had nothing to worry about. Hannah was very intelligent, and despite growing up middle class at most, she was the second in command of a high priority security firm. The two of them were planning on having children not long after they married the following year.

Naomi couldn’t be happier that her son was able to find a respectable woman and start a family to continue the family name.

*~*~*~*~*~*

Lucifer was the next to arrive home. She hadn’t seen him the previous Christmas due to a scheduling conflict, but she was hoping to reopen communication between them this year.

Her and her second oldest had always had a slightly strained relationship, he had never responded to her trying to help him as well as Michael did. Lucifer was always one to try to break the rules just for the fun of it, but after he graduated he started taking his education and future more seriously.

“Lucifer, it’s been too long,” Naomi said, holding out her hands for a hug.

She didn’t get one, however, instead Lucifer eyed her warily and said, “What are you doing Mother, you haven’t given any of us a hug since we ‘outgrew’ them?”

She gave his statement a moment's pause before deciding she thought that it was unimportant anyways.

“So how are things Lucifer? Have there been any interesting cases lately?”

The only alteration he made to Naomi’s career planthat for him was to go into the field of Law and become a corporate lawyer at the family company, was to become a judge instead after several years practicing law.

“You know I cannot give any information about a case that is not already public knowledge Mother. And I mostly deal with minor charge dismissal cases until I move up in the ranks.”

Naomi led him into the same room that Michael and Hannah were still in. Naomi introduced her second to Hannah before looking towards him after taking a seat on one of the armchairs, “I’m just asking about your life, no need to be rude. Speaking of, how is Lillith?”

Michael snorted. Lucifer turned towards him and hissed, “Like you managed any better brother, ‘cause that sure as hell isn’t Hael.”

“Of course not dear, Michael and Hael merely didn’t last, not all relationships are bound too.” Naomi decided not to reprimand him for cursing, he was a grown man and should know better than to say such a thing. “Now where is Lillith, if I may ask?”

“Like you said Mother, some couples do not last.”

“Well I suppose that is okay. I just want you to be happy Lucifer, and I can arrange for you to meet someone else,” Naomi paused for a moment, missing Lucifer's cringe, “In fact, an old work friend of mine has a daughter not much younger than you. Oh what’s her name, Ruby?”

“Oh Mother I think Lucy here is just fine when it comes to dating,” Michael smiled at Lucifer, “Why don’t you tell her just how great things went with _Kelly?”_

Lucifer looked like he was about to protest but Naomi cut him off, “Who is this Kelly? Are you dating her, why didn’t you bring her, if not I can still help you find someone?”

“Yes, I dated her for a while, she was great, but things just didn’t work out,” Lucifer sighed, “We are still close though.”

“Why?” Naomi asked, “Why are you still close to this woman if you are not interested in pursuing a relationship with her, that will hinder any future dating opportunities.”

“I am not exactly interested in dating, at least for the foreseeable future.” Lucifer paused not meeting the eyes of anyone in the room. “Kelly is expecting our child, and I, while I’m not with Kelly, will be a part of my son's life.”

“Split custody? Why ever would you do that, you can just sue for full and bring my grandbaby back here.”

“And just uproot my whole life in Atlanta? Mother be reasonable, Kelly and I have worked out many of the logistics already. We have a schedule set for him, and we agreed on all of the major early life decisions; he’ll be raised as much as possible by the two of us, we don’t want him to just be raised by nannies or babysitters, we aren’t raising him in any specific faith, and he will attend a public school in a good district.”

“Well,” Naomi clenched her jaw, “You seem to have worked this all out haven’t you?”

“Yes Mother, we want what is best for him. Our relationship, or lack thereof, should not affect his life substantially.”

“I’ll still be able to see him though, right? And bring him to Mass with me, I want my grandson to be raised properly in faith.”

“Mother, we can discuss this later If you so wish, but Kelly and I agree that he should choose whatever religion he so wishes. And if you must know, Kelly plans on taking him to the non denominational church that she and her parents attend.”

She continued to worry about her grandson even after they changed the topic of conversation to a man named Crowley that Michael ran into, apparently he was a judge that Lucifer had met before.

Naomi planned to help her son raise her first grandson in whatever way she needed, even if Lucifer didn’t appreciate it at first.

*~*~*~*~*~*

Gabriel arrived not long after Lucifer. Of her two middle children, who most people know are the most problematic, Gabriel was more subtle about his rebellion. He rarely went directly against what Naomi would tell him to do, but he would make his displeasures about it known.

Well she thought he was less obvious about defying her at least.

She left Lucifer and Michael in the living room, where they soon moved to after Lucifer’s arrival, with Hannah who was holding up a conversation about golf reasonably well.

Gabriel was already inside when she arrived. He had haphazardly tossed his polished shoes towards the rack and was eying her whilst leaning against a wall.

He at least had the decency to wear a suit, she supposed, even if the expensive tux was unbuttoned and without a tie.

“Hello Gabriel, I am happy you could join us this year,” Naomi greeted, not bothering with the hug after Lucifer’ comment.

“Hiya Ma,” Gabriel’s informalities continued into his speech so it seemed.

Naomi kept a straight face as best as she could before turning to the Asian woman standing beside him. “And who might this be?” She asked politely.

Gabriel smirked, “Well this is Kali Sharma, she’s my girlfriend of five months, she comes from a rich Indian family, she’s Hindu, and if we stay together we plan on not having children. Any questions?”

Gabriel’s brashness surprised her. But best to get all less stellar information on the table from the beginning.

It didn’t bother her that Gabriel was with someone from another country, it probably wouldn’t last anyways based on Gabriel's relationship history, but she supposed having a rich wife would help Gabriel have good contacts within the wealthier parts of the world.

She invited them inside and made introductions once they arrived in the living room. She was to first strike up a new conversation by asking, “So Kali, do you perhaps know a man by the name of Mercury Blood? I know he’s well known among the upper class, especially those in the medical field.”

“He is actually a family friend, I was visiting his hospital when I met Gabriel.”

“Gabriel this is excellent,” Naomi said, “He’s one of the top doctors at Massachusetts General, you’ll be able to get an internship there no problem. Have you heard back from any of the places you applied to yet”

“Actually Mother, I am going to finish my last year of med school but after that I’m opening a candy shop in Maine.”

“Man and I thought she was going to be pissed at me,” Lucifer laughed.

Naomi stared at him, as did Michae,l but she was the first to speak, “Gabriel you cannot be serious.”

“I am Mother, deadly,” He had an expression on his face that was far from his usual smirk, “I am done with you controlling my life. I never wanted to be a doctor in the first place, and I only met Kali at the hospital because I was so hungover that I needed my stomach pumped.”

Lucifer laughed louder now, “Gabe, this is great. All of this, I’m loving the flagrant disobedience, definitely my style. I’m proud.”

“Actually this is my style. Thank you very much. Because I for one don’t need to run home to Mommy every time something inconsequential goes wrong in my life.” Gabriel looked between his two older brothers pointedly.

“Geez, a little harsh there little bro,” Lucifer muttered, and Michael looked at his shoes.

“I suppose,” Naomi said stiltily, “That this is your decision Gabriel, but you should know that if you ever need anything I will always be here to help you.”

Gabriel rolled his eyes, “I have never needed your ‘help’ before Mother, and I shall avoid it at all costs in the future.”

Naomi returned her attention to Michael, trying to keep her wits about her. So far all three of her sons have ignored her attempts at helping and have made mistakes they will regret later on. Naomi could only hope that in the case of Gabriel he would figure out his mistake before graduating.

And she would hope that the recommendation letters she requested from several important people would make it to the best hospitals along with the applications she commissioned another medical student to write.

*~*~*~*~*~*

She was thankful when the doorbell rang signalling Castiel’ arrival. Her youngest was always very obedient, he never questioned the decisions she helped him make as he was growing up or even into adulthood. She hadn’t spoken at him as much in recent years as she had previous ones, but he was still on the path she set for him.

She was about to excuse herself to let Castiel in but Gabriel jumped up, “I’ll come greet him with you.”

Lucifer made a mildly disgusted face. “Why would you do that?” He asked.

“Trust me bro, you’re gonna love this.”

Lucifer conceded, as did Michael. The four Miltons made their way to the entry, leaving Hannah and Kali alone for a few minutes.

Naomi found herself worried that Castiel too may have disobeyed her, but she had more trust in her youngest than that. Castiel was a year behind Gabriel in school so he was two years away from graduating from Kansas Christian College with a graduate degree in religious studies; he was planning on becoming a professor at that very college.

It was unpleasant having her youngest so far away, Michael was the second furthest away in Georgia but that was still less than a day's drive away.

She still knew Castiel though, a little extra difference wasn’t going to change him dramatically.

When she opened the door she was surprised to see Castiel, who had always dressed quite formally especially at important events, wearing just dress pants and a plain blue button down.

“Hello Mother,” He greeted before Naomi had the chance. “It’s lovely to see you.”

“You as well,” She responded, almost absentmindedly.

“Well shit,” Lucifer said, he was on the porch now, looking over the rail to the older black car in the driveway not twenty feet from them. “When did you develop taste, Cassie?”

“It is quite a nice car,” Michael agreed.

Gabriel snickered, from behind her still in the house. “It’s not his car,” Gabriel said with enough emphasis to draw three pairs of unsuspecting eyes back away from said car.

Footsteps hit the three stairs leading up to the deck after Gabriel was silent for a moment.

“The car belongs to me,” A deep slightly accented voice said.

Naomi looked past Lucifer and Michael to see a handsome man, probably in his late twenties, standing closely beside Castiel. “Who might you be?” She asked in a less than polite manner.

The man, who was dressed similar to Castiel in dress pants and a green button up, extended a hand towards her with an easy smile. “My name’s Dean Winchester ma’am,” He drawled, his accent minutely more prominent.

“Yes, that’s wonderful,” She said, cautiously shaking Dean’s hand, “And why might you be here Dean?”

Gabriel laughed under his breath and responded to Michael and Lucifer’s questioning looks by saying, “Here we go.”

“Mother,” Castiel said, stepping forward, “Dean will be joining us for Christmas this year, seeing as you allow significant others to attend.”

No one said anything for several moments, Castiel’s face remained serious even after Gabriel and Dean broke out into full on laughter.

“Castiel what is this?” Naomi asked, confusion and anger lacing her voice.

“‘This’ is my husband who will be joining us for dinner, unless you wish for us to leave,” Castiel’s voice remained unwavering as he stared down Naomi.

Naomi felt her jaw drop, her usual control over her face and emotions had left her in that moment.

Dean and Gabriel had since stopped, or quieted in the latter’s case, their laughter, but Lucifer let out a full body laugh that bordered on crackle. “Fucking Lord, little bro,” He clapped a hand on Castiel’s shoulder, “Cassie just won Christmas.”

Naomi’s brain had mostly caught up to the conversation when she looked to Gabriel and asked, “So you knew about this?” He nodded, “And you just let it happen?”

“I would hardly call being his Best Man at the wedding ‘letting it happen’, but whatever floats your boat, Mother.”

“Castiel,” She looked at her youngest son in an angered state, “You should know something like this will never go if you want to be a professor at Kansas Christian.”

“Then it’s a good thing I don’t go there anymore.” At her appalled face, Castiel continued, “I transferred after the end of my freshmen year over to KU.”

“And you knew about this?” She whirled back on Gabriel.

“Not the whole time, but I found out about a year ago.” Gabriel gave her a look somewhere between bored and annoyed.

“What’s going on?” Hannah appeared in the doorway behind Gabriel.

Naomi allowed Michael a moment to answer but he appeared to be very intently staring at Dean’s car.

“This is my son Castiel,” Naomi pointed to her youngest, and terse continued, “And his _husband.”_

“Glad you made it Dean, this party was just getting a little too rich,” Kali said teasingly.

“I’m never above charming myself into somewheres above my paygrade,” Dean remarked.

Gabriel and Castiel each told their partner to behave before the youngest said, “Now that introductions have been made, we can all enjoy a lovely Christmas dinner.”

And lovely it was not.

Naomi watched as Dean made heart eyes at Cas across the table (and vice-versa), Gabriel talked about his candy shop plans, Lucifer and Kali discussed religion on the basis of raising a child, and Hannah and Michael discussed wedding preparations with her apparently married son.

Naomi didn’t help her sons as well as she thought; Michael wasn’t letting her help him with his marriage, Lucifer was bringing a child into an already broken home, Gabriel was throwing his career (and probably life) down the drain for a pipe dream, and Castiel was married to some (as she found out) mechanic from small town Kansas and ignored the opportunity to teach at on of the most prominent religious schools in the country.

*~*~*~*~*~*

Not that it should be necessary to say, but Naomi rarely saw any of her children outside of Christmas after that. 

Michael she occasionally would see at the odd company party she would attend.

Lucifer would bring Jack around every May right after his birthday.

She visited Gabriel’s shop, Trixster’s, once, he let her try a holy oil brownie (it tasted like old ash).

And once, she ran into Dean at a vintage car show she was visiting with an old friend, he was not overly pleased when she expressed her surprise at his presence there (Castiel wasn’t either).

**Author's Note:**

> This was honestly supposed to be a quick one shot, less than 2k, but it sort of grew. Now I've thought more about the storylines leading up to this and all of that, and I'm strongly considering doing a prequel of sorts from Cas' POV (HS and College, meeting and marrying Dean, ect) and maybe one about Cas and Gabe reconnecting. So let me know if you'd like something like that down below.
> 
> This is unbetaed but I might update later.


End file.
